Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and clomazone

ABSTRACT

Provided herein are synergistic herbicidal compositions containing (a) a compound of formula (I): 
                         
or an agriculturally acceptable salt or ester thereof and (b) clomazone. The compositions and methods provided herein control undesirable vegetation, e.g., in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) and rights of way (ROW).

PRIORITY CLAIM

This patent application claims the benefit of U.S. provisional patentapplication No. 61/675,056, filed on Jul. 24, 2012, which isincorporated herein by reference in its entirety.

FIELD

Provided herein are herbicidal compositions comprising (a)4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylicacid or an agriculturally acceptable ester or salt thereof and (b)clomazone. Provided herein are also methods of controlling undesirablevegetation comprising applying (a)4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylicacid or an agriculturally acceptable ester or salt thereof and (b)clomazone.

BACKGROUND

The protection of crops from weeds and other vegetation which inhibitcrop growth is a constantly recurring problem in agriculture. To helpcombat this problem, researchers in the field of synthetic chemistryhave produced an extensive variety of chemicals and chemicalformulations effective in the control of such unwanted growth. Chemicalherbicides of many types have been disclosed in the literature and alarge number are in commercial use. However, there remains a need forcompositions and methods that are effective in controlling undesirablevegetation.

SUMMARY

A first embodiment of the invention provided herein includes herbicidalcompositions comprising an herbicidally effective amount of (a) acompound of the formula (I)

or an agriculturally acceptable salt or ester thereof, and (b)clomazone.

A second embodiment includes the mixture of the first embodiment inwhich of formula (I), is present in the form of at least one of thefollowing forms: a carboxylic acid, a carboxylate salt, an aralkyl, analkyl ester, an unsubstituted benzyl, a substituted benzyl, a C₁₋₄alkyl, an n-butyl ester or a benzyl ester.

A third embodiment includes the mixture according to the first or secondembodiments wherein the weight ratio of the compound of formula (I) toclomazone given in units of gae/ha to gai/ha or gae/ha to gae/ha isselected from the group of ranges of ratios and ratios consisting of:from about 1:153 to 1:0.8, 1:12.8, 1:25.6, 1:51.1, 1:3.2, 1:6.4, 1:14,1:28, 1:38, 1:6.25, 1:20, 1:7, 1:14, 1:26, 1:12.8, 1:84, and 1:773 to6:1.

A fourth embodiment includes methods of controlling undesirablevegetation comprising the step of applying or otherwise contactingvegetation and/or soil, and/or water with a herbicidally effectiveamount of at least one mixture according to the first through the thirdembodiments.

A fifth embodiment includes methods according to the fourth embodimentwherein undesirable vegetation is controlled by practicing at least oneof the methods in a least one member of the group consisting of: indirect-seeded, water-seeded, and/or transplanted rice, cereals, wheat,barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseedrape, canola, sugar beet, soybean, cotton, pineapple, pastures,grasslands, rangelands, fallowland, turf, tree and vine orchards,aquatics, plantation crops, vegetables, industrial vegetation management(IVM), or rights-of-way (ROW).

A sixth embodiment includes methods according to the fourth and/or fifthembodiments wherein a herbicidally effective amount of the mixture isapplied either pre- or post-emergently to at least one of the following:a crop, a field, a ROW, or a rice paddy.

A seventh embodiment includes methods according to the fourth throughthe sixth embodiments wherein the undesirable vegetation may becontrolled by practicing at least one of the methods in plants that areresistant or tolerant to at least one agent or an agent that acts by atleast one mode of action selected from the group consisting of: inglyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthaseinhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-,phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transportinhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-,phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-,imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-,triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactatesynthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoenedesaturase inhibitor-, carotenoid biosynthesis inhibitor-,protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesisinhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chainfatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-,photosystem I inhibitor-, photosystem II inhibitor-, protoporphyrinogenoxidase (PPO) inhibitor-, triazine-, or bromoxynil.

An eighth embodiment includes a at least one method according to thefourth through the seventh embodiments wherein a plant that is resistantor tolerant to at least one herbicide is treated, and where theresistant or tolerant crop possesses multiple or stacked traitsconferring tolerance to multiple herbicides or inhibitors of multipleherbicide modes of action, in some embodiments the treated plant thatexpresses resistance to a herbicide is a itself undesirable vegetation.

A ninth embodiment includes methods according to the eighth embodiment,wherein the resistant or tolerant weed is a biotype with resistance ortolerance to multiple herbicides, multiple chemical classes, inhibitorsof multiple herbicide modes-of-action, or via multiple resistancemechanisms.

A tenth embodiment includes at least one of the methods according to theeighth or ninth embodiments, wherein the resistant or tolerantundesirable plant is a biotype resistant or tolerant to at least oneagent that acts by at least one mode of action selected from the groupconsisting of: acetolactate synthase (ALS) inhibitors or acetohydroxyacid synthase (AHAS), photosystem II inhibitors, acetyl CoA carboxylase(ACCase) inhibitors, synthetic auxins, auxin transport inhibitors,photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP)synthase inhibitors, microtubule assembly inhibitors, fatty acid andlipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors,carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA)inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetaseinhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors,mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides withmultiple modes-of-action, quinclorac, arylaminopropionic acids,difenzoquat, endothall, or organoarsenicals.

An eleventh embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one mixture according to the first or secondembodiments wherein the amount of the mixture is applied at a rate,expressed in ai/ha of clomazone selected from the group of rates andranges of rates consisting of, about: 1, 2, 25, 56, 112, 224, 448, 670,840, and the range 1:1000.

A twelfth embodiment includes methods according to the first, third, andeleventh embodiments wherein the controlled plant is at least one plantselected from the group consisting of: DIGSA, LEFCH, IPOHE, ECHCG,ECHCO, CYPRO, CYPDI, and SCPMA, still other embodiments includecontrolling plants from the genera consisting of: Digitaria, Leptochloa,Ipomoea, Echinochloa, Bolboschoenus, and Cyperus.

Provided herein are herbicidal compositions comprising a herbicidallyeffective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester of thereof, and (b)clomazone. The compositions may also contain an agriculturallyacceptable adjuvant or carrier.

Provided herein are also methods of controlling undesirable vegetationcomprising applying (a) a compound of formula (I) or an agriculturallyacceptable ester or salt thereof and (b) clomazone or an agriculturallyacceptable salt or ester thereof.

DETAILED DESCRIPTION Definitions

As used herein, the compound of formula (I) has the following structure:

The compound of formula (I) can be identified by the name4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylicacid and has been described in U.S. Pat. No. 7,314,849 (B2), which isincorporated herein by reference in its entirety. Exemplary uses of thecompound of the formula (I) include controlling undesirable vegetation,including grass, broadleaf and sedge weeds, in multiple non-crop andcropping situations.

As used herein, clomazone is2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone and possessesthe following structure:

Its herbicidal activity is exemplified in Tomlin, C., ed. A WorldCompendium The Pesticide Manual. 15^(th) ed. Alton: BCPC Publications,2009. Exemplary uses of clomazone include its use for pre-emergence,pre-plant incorporated, or very early post-emergence control ofsmall-seeded broadleaf and annual grass weeds, e.g., in rice, soybean,peas, maize, oilseed rape, sugar cane, cassava, pumpkins, potatoes,tobacco and other vegetables. Clomazone can be applied, e.g., pre-plantincorporated or pre-emergence to the soil, or as an early post-emergencetreatment to undesirable vegetation. As another example, clomazone canbe applied pre-emergence to the soil before or after planting rice andinto flooded rice paddies/fields to control, e.g., annual grasses.

As used herein, herbicide means a compound, e.g., active ingredient thatkills, controls or otherwise adversely modifies the growth of plants.

As used herein, a herbicidally effective or vegetation controllingamount is an amount of active ingredient which causes an adverselymodifying effect to the vegetation e.g., causing deviations from naturaldevelopment, killing, effecting regulation, causing desiccation, causingretardation, and the like.

As used herein, controlling undesirable vegetation means preventing,reducing, killing, or otherwise adversely modifying the development ofplants and vegetation. Described herein are methods of controllingundesirable vegetation through the application of certain herbicidecombinations or compositions. Methods of application include, but arenot limited to applications to the vegetation or locus thereof, e.g.,application to the area adjacent to the vegetation, as well aspre-emergence, post-emergence, foliar (broadcast, directed, banded,spot, mechanical, over-the-top, or rescue), and in-water applications(emerged and submerged vegetation, broadcast, spot, mechanical,water-injected, granular broadcast, granular spot, shaker bottle, orstream spray) via hand, backpack, machine, tractor, or aerial (airplaneand helicopter) application methods.

As used herein, plants and vegetation include, but are not limited to,germinant seeds, emerging seedlings, plants emerging from vegetativepropagules, immature vegetation, and established vegetation.

As used herein, agriculturally acceptable salts and esters refer tosalts and esters that exhibit herbicidal activity, or that are or can beconverted in plants, water, or soil to the referenced herbicide.Exemplary agriculturally acceptable esters are those that are or can behydrolyzed, oxidized, metabolized, or otherwise converted, e.g., inplants, water, or soil, to the corresponding carboxylic acid which,depending on the pH, may be in the dissociated or undissociated form.

Exemplary salts include those derived from alkali or alkaline earthmetals and those derived from ammonia and amines. Exemplary cationsinclude sodium, potassium, magnesium, and ammonium cations of theformula:R¹R²R³R⁴N⁺wherein R¹, R², R³ and R⁴ each, independently represents hydrogen orC₁-C₁₂ alkyl, C₃-C₁₂ alkenyl or C₃-C₁₂ alkynyl, each of which isoptionally substituted by one or more hydroxy, C₁-C₄ alkoxy, C₁-C₄alkylthio or phenyl groups, provided that R¹, R², R³ and R⁴ aresterically compatible. Additionally, any two of R¹, R², R³ and R⁴together may represent an aliphatic difunctional moiety containing oneto twelve carbon atoms and up to two oxygen or sulfur atoms. Salts canbe prepared by treatment with a metal hydroxide, such as sodiumhydroxide, with an amine, such as ammonia, trimethylamine,diethanolamine, 2-methylthiopropylamine, bisallylamine,2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine orwith a tetraalkylammonium hydroxide, such as tetramethylammoniumhydroxide or choline hydroxide.

Exemplary esters include those derived from C₁-C₁₂ alkyl, C₃-C₁₂alkenyl, C₃-C₁₂ alkynyl or C₇-C₁₀ aryl-substituted alkyl alcohols, suchas methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol,butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol,cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzylalcohols may be substituted with from 1-3 substituents independentlyselected from halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy. Esters can beprepared by coupling of the acids with the alcohol using any number ofsuitable activating agents such as those used for peptide couplings suchas dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); byreacting the acids with alkylating agents such as alkylhalides oralkylsulfonates in the presence of a base such as triethylamine orlithium carbonate; by reacting the corresponding acid chloride of anacid with an appropriate alcohol; by reacting the corresponding acidwith an appropriate alcohol in the presence of an acid catalyst or bytransesterification.

Compositions and Methods

Provided herein are herbicidal compositions comprising a herbicidallyeffective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester of thereof, and (b)clomazone.

Provided herein are also methods of controlling undesirable vegetationcomprising contacting the vegetation or locus thereof, i.e., the areaadjacent to the vegetation with or applying to the soil or water toprevent the emergence or growth of vegetation a herbicidally effectiveamount of the compound of formula (I) or agriculturally acceptable saltor ester thereof and (b) clomazone. In certain embodiments, the methodsemploy the compositions described herein.

Furthermore, in some embodiments, the combination of compound (I) oragriculturally acceptable salt or ester thereof and clomazone exhibitssynergism, e.g., the herbicidal active ingredients are more effective incombination than when applied individually. Synergism has been definedas “an interaction of two or more factors such that the effect whencombined is greater than the predicted effect based on the response ofeach factor applied separately.” Senseman, S., ed. Herbicide Handbook.9^(th) ed. Lawrence: Weed Science Society of America, 2007. In certainembodiments, the compositions exhibit synergy as determined by theColby's equation. Colby, S. R. 1967. Calculation of the synergistic andantagonistic response of herbicide combinations. Weeds 15:20-22.

In certain embodiments of the compositions and methods described herein,the compound of formula (I), i.e., the carboxylic acid, is employed. Incertain embodiments, a carboxylate salt of the compound of formula (I)is employed. In certain embodiments, an aralkyl or alkyl ester isemployed. In certain embodiments, a benzyl, substituted benzyl, or C₁₋₄alkyl, e.g., n-butyl ester is employed. In certain embodiments, thebenzyl ester is employed.

In some embodiments, the compound of formula (I) or salt or esterthereof and clomazone are formulated in one composition, tank mixed,applied simultaneously, or applied sequentially.

Herbicidal activity is exhibited by the compounds when they are applieddirectly to the plant or to the area adjacent to the plant at any stageof growth. The effect observed depends upon the plant species to becontrolled, the stage of growth of the plant, the application parametersof dilution and spray drop size, the particle size of solid components,the environmental conditions at the time of use, the specific compoundemployed, the specific adjuvants and carriers employed, the soil type,and the like, as well as the amount of chemical applied. These and otherfactors can be adjusted to promote non-selective or selective herbicidalaction. In some embodiments, the compositions described herein areapplied as a post-emergence application, pre-emergence application, orin-water application to flooded paddy rice or water bodies (e.g., ponds,lakes and streams), to relatively immature undesirable vegetation toachieve the maximum control of weeds.

In some embodiments, the compositions and methods provided herein areutilized to control weeds in crops, including but not limited todirect-seeded, water-seeded and transplanted rice, cereals, wheat,barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseedrape, canola, sugar beet, soybean, cotton, pineapple, pastures,grasslands, rangelands, fallowland, turf, tree and vine orchards,aquatics, plantation crops, vegetables, industrial vegetation management(IVM) and rights of way (ROW).

In certain embodiments, the compositions and methods provided herein areutilized to control weeds in rice. In certain embodiments, the rice isdirect-seeded, water-seeded, or transplanted rice.

The compositions and methods described herein may be used to controlundesirable vegetation in glyphosate-tolerant-,5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-tolerant-,glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-,dicamba-tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-,auxin-tolerant-, auxin transport inhibitor-tolerant-,aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-,phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase)inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-,pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-,sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS)or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerant-,phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesisinhibitor-tolerant-, protoporphyrinogen oxidase (PPO)inhibitor-tolerant-, cellulose biosynthesis inhibitor-tolerant-, mitosisinhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chainfatty acid inhibitor-tolerant-, fatty acid and lipid biosynthesisinhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem IIinhibitor-tolerant-, triazine-tolerant- and bromoxynil-tolerant-crops(such as, but not limited to, soybean, cotton, canola/oilseed rape,rice, cereals, corn, sorghum, sunflower, sugar beet, sugarcane, turf,etc), for example, in conjunction with glyphosate, EPSP synthaseinhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxyauxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors,aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCaseinhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,dimethoxy-pyrimidines, triazolopyrimidine sulfonamides,sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPDinhibitors, phytoene desaturase inhibitors, carotenoid biosynthesisinhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosisinhibitors, microtubule inhibitors, very long chain fatty acidinhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem Iinhibitors, photosystem II inhibitors, triazines, and bromoxynil. Thecompositions and methods may be used in controlling undesirablevegetation in crops possessing multiple or stacked traits conferringtolerance to multiple chemistries and/or inhibitors of multiple modes ofaction. In some embodiments, the compound of formula (I) or salt orester thereof and complementary herbicide or salt or ester thereof areused in combination with herbicides that are selective for the cropbeing treated and which complement the spectrum of weeds controlled bythese compounds at the application rate employed. In some embodiments,the compositions described herein and other complementary herbicides areapplied at the same time, either as a combination formulation or as atank mix, or sequentially.

The compositions and methods may be used in controlling undesirablevegetation in crops possessing agronomic stress tolerance (including butnot limited to drought, cold, heat, salt, water, nutrient, fertility,pH), pest tolerance (including but not limited to insects, fungi andpathogens) and crop improvement traits (including but not limited toyield; protein, carbohydrate, or oil content; protein, carbohydrate, oroil composition; plant stature and plant architecture).

The compositions and methods provided herein are utilized to controlundesirable vegetation. Undesirable vegetation includes, but is notlimited to, undesirable vegetation that occurs in rice, cereals, wheat,barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseedrape, canola, sugar beet, soybean, cotton, pineapple, pastures,grasslands, rangelands, fallowland, turf, tree and vine orchards,aquatics, plantation crops, vegetables, industrial vegetation management(IVM) and rights of way (ROW).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in rice. In certain embodiments, the undesirablevegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloaplatyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloaspecies (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass,ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV),Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides(Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola(Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon(Stapf) Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya(Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb.(saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinesesprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (beardedsprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazonsprangletop, LEFPA), Oryza species (red and weedy rice, ORYSS), Panicumdichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatumPoir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W. D.Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus difformisL. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU),Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (riceflatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Cyperusserotinus Rottb./C. B. Clarke (tidalmarsh flatsedge, CYPSE), Eleocharisspecies (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush,FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb.(Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla orSchoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectusmucronatus L. (ricefield bulrush, SCPMU), Aeschynomene species,(jointvetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb.(alligatorweed, ALRPH), Alisma plantago-aquatica L. (commonwaterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths,AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelinabenghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk.(American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl(ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleafmudplantain, HETRE), Ipomoea species (morningglories, IPOSS), Ipomoeahederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L.)Pennell (low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigialinifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigiaoctovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC),Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoriavaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannianudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L.,(Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb,POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotalaindica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species,(arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hempsesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in cereals. In certain embodiments, theundesirable vegetation is Alopecurus myosuroides Huds. (blackgrass,ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L.(wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Loliummultflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz.(littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN),Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU),Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthusretroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS),Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.)Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw,GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureumL. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile,MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT),Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wildbuckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapisspecies (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellariamedia (L.) Vill. (common chickweed, STEME), Veronica persica Poir.(Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR),or Viola tricolor L. (wild violet, VIOTR).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in range and pasture, fallowland, IVM and ROW. Incertain embodiments, the undesirable vegetation is Ambrosiaartemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sicklepod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed,CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulusarvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot,DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriolaL./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhornplantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Sidaspinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard,SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidagospecies (goldenrod, SOOSS), Taraxacum officinale G. H. Weber ex Wiggers(dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urticadioica L. (common nettle, URTDI).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation found in row crops, tree and vine crops, andperennial crops. In certain embodiments, the undesirable vegetation isAlopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wildoat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf)R. D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. exA. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R. D.(beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloaplatyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southernsandbar, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass,DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloacrus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum(L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn. (goosegrass,ELEIN), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicumdichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L.(wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail,SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghumhalepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moenchssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellownutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilontheophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds andamaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL),Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L.(giant ragweed, AMBTR), Anoda cristata (L.) Schlecht. (spurred anoda,ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L.(hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata(Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed, BOILF),Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium albumL. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canadathistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE),Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot,DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbiahirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI),Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensisL. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeroncanadensis L. or Conyza canadensis (L.) Cronq. (Canadian fleabane,ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL),Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia(L.) Griseb. (smallflower morningglory, IAQTA), Ipomoea hederacea (L.)Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (whitemorningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce,LACSE), Portulaca oleracea L. (common purslane, POROL), Richardiaspecies (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L.(prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR),Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridaxprocumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (commoncocklebur, XANST).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in turf. In certain embodiments, the undesirablevegetation is Bellis perennis L. (English daisy, BELPE), Cyperusesculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodiavirginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge,EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellataL. (dollarweed, HYDUM), Kyllinga species (kylling a, KYLSS), Lamiumamplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan(doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L.(broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhorn/narrowleafplantain, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumexobtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew.(Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed,STEME), Taraxacum officinale G. H. Weber ex Wiggers (dandelion, TAROF),Trifolium repens L. (white clover, TRFRE), or Viola species (wildviolet, VIOSS).

In some embodiments, the compositions and methods provided herein areutilized to control undesirable vegetation consisting of grass,broadleaf and sedge weeds. In certain embodiments, the compositions andmethods provided herein are utilized to control undesirable grass,broadleaf and sedge vegetation including but not limited toBolboschoenus, Cyperus, Digitaria, Echinochloa, Ipomoea, and Leptochloa,

In some embodiments, the combination of compound (I) or agriculturallyacceptable ester or salt thereof and clomazone are used to control,including but not limited to large crabgrass (Digitaria sanguinalis),barnyardgrass (Echinochloa crus-galli), jungle rice (Echinochloacolona), ivyleaf morningglory (Ipomoea hederacea), Chinese sprangletop(Leptochloa chinensis), smallflower umbrella sedge (Cyperus difformis),purple nutsedge (Cyperus rotundus) and sea clubrush (Bolboschoenusmaritimus or Schoenoplectus maritimus).

The compounds of formula I or agriculturally acceptable salt or esterthereof may be used to control herbicide resistant or tolerant weeds.The methods employing the combination of a compound of formula I oragriculturally acceptable salt or ester thereof and the compositionsdescribed herein may also be employed to control herbicide resistant ortolerant weeds. Exemplary resistant or tolerant weeds include, but arenot limited to, biotypes resistant or tolerant to acetolactate synthase(ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g.,imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,dimethoxy-pyrimidines, triazolopyrimidine sulfonamides,sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g.,phenylcarbamates, pyridazinones, triazines, triazinones, uracils,amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetylCoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates,cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g., benzoicacids, phenoxycarboxylic acids, pyridine carboxylic acids, quinolinecarboxylic acids), auxin transport inhibitors (e.g., phthalamates,semicarbazones), photosystem I inhibitors (e.g., bipyridyliums),5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors (e.g.,glyphosate), glutamine synthetase inhibitors (e.g., glufosinate,bialafos), microtubule assembly inhibitors (e.g., benzamides, benzoicacids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors(e.g., carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g.,acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acidand lipid synthesis inhibitors (e.g., phosphorodithioates,thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogenoxidase (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides,oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones,thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g.,clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors(e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones,pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors(e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulosebiosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac,triazolocarboxamides), herbicides with multiple modes-of-action such asquinclorac, and unclassified herbicides such as arylaminopropionicacids, difenzoquat, endothall, and organoarsenicals. Exemplary resistantor tolerant weeds include, but are not limited to, biotypes withresistance or tolerance to multiple herbicides, biotypes with resistanceor tolerance to multiple chemical classes, biotypes with resistance ortolerance to multiple herbicide modes-of-action, and biotypes withmultiple resistance or tolerance mechanisms (e.g., target siteresistance or metabolic resistance).

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with clomazone. With respect to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to clomazone is within the ranges of from about 1:773 toabout 6:1 or from about 1:850 to about 3:1. In certain embodiments, theweight ratio of the compound of formula (I) or salt or ester thereof toclomazone is within the range of from about 1:153 to about 1:1 or about1:32 to about 1:1. In certain embodiments, the weight ratio of thecompound of formula (I) or salt or ester thereof to clomazone is withinthe range of from about 1:1.6 to about 1:52 or about 1:16 to about 1:10.In certain embodiments, the weight ratio of the compound of formula (I)or salt or ester thereof to clomazone is within the ranges of from about1:1.6 to about 1:51, or 1:3.2 to about 1:51. In certain embodiments, thecompositions provided herein comprise the compound of formula (I) or itsbenzyl ester and clomazone. In one embodiment, the composition comprisesthe compound of formula (I) and clomazone, wherein the weight ratios ofthe compound of formula (I) to clomazone is about 1:773 to about 6:1, orabout 1:3.2 to about 1:56. In one embodiment, the composition comprisesthe benzyl ester of the compound of formula (I) and clomazone, whereinthe weight ratio of the benzyl ester of the compound of formula (I) toclomazone is about 1:153 to about 1:1, or about 1:3.2 to about 1:56.With respect to the methods, in certain embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation a composition described herein. In some embodiments, thecomposition is applied at an application rate of from about 52 or about102 grams active ingredient per hectare (gai/ha) to about 2,100 gai/habased on the total amount of active ingredients in the composition. Incertain embodiments, the composition is applied at an application rateof from about 60 grams active ingredient per hectare (gai/ha) to about734 gai/ha or 110 gai/ha to about 1,000 gai/ha based on the total amountof active ingredients in the composition. In some embodiments, themethods comprise contacting the undesirable vegetation or locus thereofor applying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andclomazone, e.g., sequentially or simultaneously. In some embodiments,clomazone is applied at a rate from about 100 to about 1,700 or about 50gai/ha to about 1,700 gai/ha and the compound of formula (I) of salt orester thereof is applied at a rate from about 2 gae/ha to about 300gae/ha. In some embodiments, clomazone is applied at a rate from about54 gai/ha to about 1,000 gai/ha or from about 28 gai/ha to about 448gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 g acid equivalent per hectare (gae/ha) toabout 200 gae/ha or to about 706 gae/ha. In some embodiments, clomazoneis applied at a rate from about 56 gai/ha to about 670 gai/ha or toabout 224 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 4.38 g acid equivalent perhectare (gae/ha) to about 64 gae/ha or about 4.38 gae/ha to about 35gae/ha. In certain embodiments, the methods utilize the compound offormula (I), or its benzyl ester and clomazone. In one embodiment, themethods utilize the compound of formula (I) and clomazone, wherein thecompound of formula (I) is applied at a rate of from about 4.38 g acidequivalent per hectare (gae/ha) to about 64 gae/ha, and clomazone isapplied at a rate of about 56 gai/ha to about 670 gai/ha, or (I) isapplied at a rate of from about 4.38 g acid equivalent per hectare(gae/ha) to about 64 gae/ha or about 4.38 to about 35 gae/ha, andclomazone is applied at a rate of about 56 gai/ha to about 670 gai/ha orabout 56 gai/ha to about 224 gae/ha. In one embodiment, the methodsutilize the benzyl ester of the compound of formula (I) and clomazone,wherein the benzyl ester of the compound of formula (I) is applied at arate of from about 4.38 g acid equivalent per hectare (gae/ha) to about64 gae/ha, and clomazone is applied at a rate of about 56 gai/ha toabout 670 gai/ha or the benzyl ester of the compound of formula (I) andclomazone, wherein the benzyl ester of the compound of formula (I) isapplied at a rate of from about 4.38 g acid equivalent per hectare(gae/ha) to about 64 gae/ha, and clomazone is applied at a rate of about56 gai/ha to about 670 gai/ha. In some embodiments, the methods utilizethe benzyl ester of the compound of Formula (I) and clomazone, where thebenzyl ester of compound of Formula (I) is applied at a rate from about4.38 gae/ha to about 17.5 gae/ha and clomazone is applied at a rate ofabout 56 gai/ha to about 224 gai/ha. In certain embodiments, the methodsand compositions utilizing the compound of formula (I) or salt or esterthereof in combination with clomazone are used to control CYPDI, CYPRO,DIGSA, ECHCG, ECHCO, IPOHE, LEFCH and SCPMA.

The components of the mixtures described herein can be applied eitherseparately or as part of a multipart herbicidal system.

The mixtures described herein can be applied in conjunction with one ormore other herbicides to control a wider variety of undesirablevegetation. When used in conjunction with other herbicides, thecomposition can be formulated with the other herbicide or herbicides,tank mixed with the other herbicide or herbicides or appliedsequentially with the other herbicide or herbicides. Some of theherbicides that can be employed in conjunction with the compositions andmethods described herein include, but are not limited to: 4-CPA; 4-CPB;4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB;3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB;acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor,alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin,amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid,amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron,asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne,barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin,benfuresate, bensulfuron-methyl, bensulide, benthiocarb,bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon,benzofenap, benzofluor, benzoylprop, benzthiazuron, bialaphos,bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil,bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon,butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron,butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole,calcium chlorate, calcium cyanamide, cambendichlor, carbasulam,carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC,chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine,chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop,chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen,chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham,chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin,cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop-propargyl,clofop, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl,CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron,cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron,cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole,cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn,di-allate, dicamba, dichlobenil, dichloralurea, dichlormate,dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, diethamquat,diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine,dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid,dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP,eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin,ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid,etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen,etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop,fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone,fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate,flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop,fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron,fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam,flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron,fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron,flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurtamone,fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen,glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosatesalts and esters, halauxifen, halauxifen-methyl, halosafen,halosulfuron-methyl, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl,hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox,imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, indanofan,indaziflam, iodobonil, iodomethane, iodosulfuron,iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine,ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin,isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben,isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox,lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines,MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet,mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop,metamitron, metazachlor, metazosulfuron, metflurazon,methabenzthiazuron, methalpropalin, methazole, methiobencarb,methiozolin, methiuron, methometon, methoprotryne, methyl bromide,methyl isothiocyanate, methyldymron, metobenzuron, metobromuron,metolachlor, metosulam, metoxuron, metribuzin, metsulfuron,metsulfuron-methyl, molinate, monalide, monisouron, monochloroaceticacid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide,naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen,nitrofluorfen, norflurazon, noruron, OCH, orbencarb,ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon,oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl,parafluoron, paraquat, pebulate, pelargonic acid, pendimethalin,penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone,pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl,phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden,piperophos, potassium arsenite, potassium azide, potassium cyanate,pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol,profluralin, profoxydim, proglinazine, prohexadione-calcium, prometon,prometryn, pronamide, propachlor, propanil, propaquizafop, propazine,propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide,prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon,pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate,pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor,pyridafol, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil,rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton,sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite,sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone,sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin,swep, SYN-523, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,terbuthylazine, terbutryn, tetrafluoron, thenylchlor, thiazafluoron,thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl,thifensulfuron, thifensulfurn-methyl, thiobencarb, tiocarbazil,tioclorim, topramezone, tralkoxydim, triafamone, tri-allate,triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba,triclopyr choline salt, triclopyr esters and amines, tridiphane,trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop,trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritactritosulfuron, vernolate, xylachlor and salts, esters, optically activeisomers and mixtures thereof.

The compositions and methods described herein, can further be used inconjunction with glyphosate, 5-enolpyruvylshikimate-3-phosphate (EPSP)synthase inhibitors, glufosinate, glutamine synthetase inhibitors,dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxintransport inhibitors, aryloxyphenoxypropionates, cyclohexanediones,phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors,imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,triazolopyrimidines, sulfonylaminocarbonyltriazolinones, acetolactatesynthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoenedesaturase inhibitors, carotenoid biosynthesis inhibitors,protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesisinhibitors, mitosis inhibitors, microtubule inhibitors, very long chainfatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors,photosystem I inhibitors, photosystem II inhibitors, triazines, andbromoxynil on glyphosate-tolerant, EPSP synthase inhibitor-tolerant,glufosinate-tolerant, glutamine synthetase inhibitor-tolerant,dicamba-tolerant, phenoxy auxin-tolerant, pyridyloxy auxin-tolerant,auxin-tolerant, auxin transport inhibitor-tolerant,aryloxyphenoxypropionate-tolerant, cyclohexanedione-tolerant,phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinone-tolerant,sulfonylurea-tolerant, pyrimidinylthiobenzoate-tolerant,triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant,ALS- or AHAS-tolerant, HPPD-tolerant, phytoene desaturaseinhibitor-tolerant, carotenoid biosynthesis inhibitor tolerant,PPO-tolerant, cellulose biosynthesis inhibitor-tolerant, mitosisinhibitor-tolerant, microtubule inhibitor-tolerant, very long chainfatty acid inhibitor-tolerant, fatty acid and lipid biosynthesisinhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem IIinhibitor-tolerant, triazine-tolerant, bromoxynil-tolerant, and cropspossessing multiple or stacked traits conferring tolerance to multiplechemistries and/or multiple modes of action via single and/or multipleresistance mechanisms. In some embodiments, the compound of formula (I)or salt or ester thereof and complementary herbicide or salt or esterthereof are used in combination with herbicides that are selective forthe crop being treated and which complement the spectrum of weedscontrolled by these compounds at the application rate employed. In someembodiments, the compositions described herein and other complementaryherbicides are applied at the same time, either as a combinationformulation or as a tank mix.

In some embodiments, the compositions described herein are employed incombination with one or more herbicide safeners, such as AD-67 (MON4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl),cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton,fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole,harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi,mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil,R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance theirselectivity. In some embodiments, the safeners are employed in rice,cereal, corn, or maize settings. In some embodiments, the safener iscloquintocet or an ester or salt thereof. In certain embodiments,cloquintocet is utilized to antagonize harmful effects of thecompositions on rice and cereals. In some embodiments, the safener iscloquintocet (mexyl).

In some embodiments, the compositions described herein are employed incombination with one or more plant growth regulators, such as2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide,α-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl alcohol,kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron,tribufos, aviglycine, ethephon, maleic hydrazide, gibberellins,gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine,isopyrimol, jasmonic acid, maleic hydrazide, mepiquat,2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol, flurprimidol,mefluidide, paclobutrazol, tetcyclacis, uniconazole, brassinolide,brassinolide-ethyl, cycloheximide, ethylene, methasulfocarb,prohexadione, triapenthenol and trinexapac.

In some embodiments, the plant growth regulators are employed in one ormore crops or settings, such as rice, cereal crops, corn, maize,broadleaf crops, oilseed rape/canola, turf, pineapple, sugarcane,sunflower, pastures, grasslands, rangelands, fallowland, tree and vineorchards, plantation crops, vegetables, and non-crop (ornamentals)settings. In some embodiments, the plant growth regulator is mixed withthe compound of formula (I), or mixed with the compound of formula (I)and clomazone to cause a preferentially advantageous effect on plants.

In some embodiments, compositions provided herein further comprise atleast one agriculturally acceptable adjuvant or carrier. Suitableadjuvants or carriers should not be phytotoxic to valuable crops,particularly at the concentrations employed in applying the compositionsfor selective weed control in the presence of crops, and should notreact chemically with herbicidal components or other compositioningredients. Such mixtures can be designed for application directly toweeds or the area adjacent to the weeds or can be concentrates orformulations that are normally diluted with additional carriers andadjuvants before application. They can be solids, such as, for example,dusts, granules, water-dispersible granules, or wettable powders, orliquids, such as, for example, emulsifiable concentrates, solutions,emulsions or suspensions. They can also be provided as a pre-mix or tankmixed.

Suitable agricultural adjuvants and carriers include, but are notlimited to, crop oil concentrate; nonylphenol ethoxylate;benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleumhydrocarbon, alkyl esters, organic acid, and anionic surfactant; C₉-C₁₁alkylpolyglycoside; phosphated alcohol ethoxylate; natural primaryalcohol (C₁₂-C₁₆) ethoxylate; di-sec-butylphenol EO-PO block copolymer;polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrate;emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate(8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99.

Liquid carriers that can be employed include water and organic solvents.The organic solvents include, but are not limited to, petroleumfractions or hydrocarbons such as mineral oil, aromatic solvents,paraffinic oils, and the like; vegetable oils such as soybean oil,rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil,corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, saffloweroil, sesame oil, tung oil and the like; esters of the above vegetableoils; esters of monoalcohols or dihydric, trihydric, or other lowerpolyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate,n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octylsuccinate, di-butyl adipate, di-octyl phthalate and the like; esters ofmono, di and polycarboxylic acids and the like. Specific organicsolvents include, but are not limited to toluene, xylene, petroleumnaphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone,trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butylacetate, propylene glycol monomethyl ether and diethylene glycolmonomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amylalcohol, ethylene glycol, propylene glycol, glycerine,N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide,liquid fertilizers and the like. In certain embodiments, water is thecarrier for the dilution of concentrates.

Suitable solid carriers include but are not limited to talc,pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr,chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay,Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice,wood flour, walnut shell flour, lignin, cellulose, and the like.

In some embodiments, the compositions described herein further compriseone or more surface-active agents. In some embodiments, suchsurface-active agents are employed in both solid and liquidcompositions, and in certain embodiments those designed to be dilutedwith carrier before application. The surface-active agents can beanionic, cationic or nonionic in character and can be employed asemulsifying agents, wetting agents, suspending agents, or for otherpurposes. Surfactants which may also be used in the present formulationsare described, inter alia, in “McCutcheon's Detergents and EmulsifiersAnnual,” MC Publishing Corp., Ridgewood, N.J., 1998 and in “Encyclopediaof Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980-81.Surface-active agents include, but are not limited to salts of alkylsulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonatesalts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkyleneoxide addition products, such as nonylphenol-C₁₈ ethoxylate;alcohol-alkylene oxide addition products, such as tridecyl alcohol-C₁₆ethoxylate; soaps, such as sodium stearate; alkyl-naphthalene-sulfonatesalts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters ofsulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate;sorbitol esters, such as sorbitol oleate; quaternary amines, such aslauryl trimethylammonium chloride; polyethylene glycol esters of fattyacids, such as polyethylene glycol stearate; block copolymers ofethylene oxide and propylene oxide; salts of mono and dialkyl phosphateesters; vegetable or seed oils such as soybean oil, rapeseed/canola oil,olive oil, castor oil, sunflower seed oil, coconut oil, corn oil,cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesameoil, tung oil and the like; and esters of the above vegetable oils, andin certain embodiments, methyl esters.

In some embodiments, these materials, such as vegetable or seed oils andtheir esters, can be used interchangeably as an agricultural adjuvant,as a liquid carrier or as a surface active agent.

Other exemplary additives for use in the compositions provided hereininclude but are not limited to compatibilizing agents, antifoam agents,sequestering agents, neutralizing agents and buffers, corrosioninhibitors, dyes, odorants, spreading agents, penetration aids, stickingagents, dispersing agents, thickening agents, freezing pointdepressants, antimicrobial agents, and the like. The compositions mayalso contain other compatible components, for example, other herbicides,plant growth regulants, fungicides, insecticides, and the like and canbe formulated with liquid fertilizers or solid, particulate fertilizercarriers such as ammonium nitrate, urea and the like.

In some embodiments, the concentration of the active ingredients in thecompositions described herein is from about 0.0005 to 98 percent byweight. In some embodiments, the concentration is from about 0.0006 to90 percent by weight. In compositions designed to be employed asconcentrates, the active ingredients, in certain embodiments, arepresent in a concentration from about 0.1 to 98 weight percent, and incertain embodiment's about 0.5 to 90 weight percent. Such compositionsare, in certain embodiments, diluted with an inert carrier, such aswater, before application. The diluted compositions usually applied toweeds or the locus of weeds contain, in certain embodiments, about0.0006 to 10.0 weight percent active ingredient and in certainembodiments contain about 0.001 to 6.0 weight percent.

The present compositions can be applied to undesirable vegetation(weeds) or the area adjacent to the weeds by the use of conventionalground or aerial dusters, sprayers, and granule applicators, by additionto irrigation or paddy water, and by other conventional means known tothose skilled in the art.

The described embodiments and following examples are for illustrativepurposes and are not intended to limit the scope of the claims. Othermodifications, uses, or combinations with respect to the compositionsdescribed herein will be apparent to a person of ordinary skill in theart without departing from the spirit and scope of the claimed subjectmatter.

EXAMPLES

Results in Examples I and II are greenhouse trial results.

Example I Evaluation of Postemergence Foliar-Applied Herbicidal Mixturesfor Weed Control in Direct-Seeded Rice

Seeds or nutlets of the desired test plant species were planted in asoil matrix prepared by mixing a loam or sandy loam soil (e.g., 28.6percent silt, 18.8 percent clay, and 52.6 percent sand, with a pH ofabout 5.8 and an organic matter content of about 1.8 percent) andcalcareous grit in an 80 to 20 ratio. The soil matrix was contained inplastic pots with a volume of 1 quart and a surface area of 83.6 squarecentimeters (cm²). When required to ensure good germination and healthyplants, a fungicide treatment and/or other chemical or physicaltreatment was applied. The plants were grown for 8-22 days in agreenhouse with an approximate 14 h photoperiod which was maintained atabout 29° C. during the day and 26° C. during the night. Nutrients(Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were applied in theirrigation solution as needed and water was added on a regular basis.Supplemental lighting was provided with overhead metal halide 1000-Wattlamps as necessary. The plants were employed for testing when theyreached the first through fourth true leaf stage.

Treatments consisted of the acid or esters of4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylicacid (Compound A), each formulated as an SC (suspension concentrate),and various herbicidal components alone and in combination. Forms ofcompound A were applied on an acid equivalent basis.

Forms of compound A (compound of formula I) tested include:

Other herbicidal components were applied on an active ingredient basisand consisted of clomazone formulated as Command® 3ME. Treatmentrequirements were calculated based upon the rates being tested, theconcentration of active ingredient or acid equivalent in theformulation, and a 12 mL application volume at a rate of 187 L/ha.

For treatments comprised of formulated compounds, measured amounts ofcompounds were placed individually in 25 mL glass vials and diluted in avolume of 1.25% (v/v) Agri-Dex® crop oil concentrated to obtain 12×stock solutions. If a test compound did not dissolve readily, themixture was warmed and/or sonicated. Application solutions were preparedby adding an appropriate amount of each stock solution (e.g., 1 mL) anddiluted to the appropriate final concentrations with the addition of 10mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that thefinal spray solutions contained 1.25+/−0.05% (v/v) crop oil concentrate.

For treatments comprised of technical compounds, weighed amounts can beplaced individually in 25 mL glass vials and dissolved in a volume of97:3 v/v acetone/DMSO to obtain 12× stock solutions. If a test compounddoes not dissolve readily, the mixture can be warmed and/or sonicated.Application solutions can be prepared by adding an appropriate amount ofeach stock solution (e.g., 1 mL) and diluted to the appropriate finalconcentrations with the addition of 10 mL of an aqueous mixture of 1.5%(v/v) crop oil concentrate so that the final spray solutions contain1.25% (v/v) crop oil concentrate. When technical materials are used, theconcentrated stock solutions can be added to the spray solutions so thatthe final acetone and DMSO concentrations of the application solutionsare 16.2% and 0.5%, respectively.

For treatments comprised of formulated and technical compounds, weighedamounts of the technical materials can be placed individually in 25 mLglass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain12× stock solutions, and measured amounts of the formulated compoundscan be placed individually in 25 mL glass vials and diluted in a volumeof 1.5% (v/v) crop oil concentrate or water to obtain 12× stocksolutions. If a test compound does not dissolve readily, the mixture canbe warmed and/or sonicated. Application solutions can be prepared byadding an appropriate amount of each stock solution (e.g., 1 mL) anddiluted to the appropriate final concentrations with the addition of anappropriate amount of an aqueous mixture of 1.5% (v/v) crop oilconcentrate so that the final spray solutions contain 1.25% (v/v) cropoil concentrate. As required, additional water and/or 97:3 v/vacetone/DMSO can be added to individual application solutions so thatthe final acetone and DMSO concentrations of the application solutionsbeing compared are 8.1% and 0.25%, respectively.

All stock solutions and applications solutions were visually inspectedfor compound compatibility prior to application. Spray solutions wereapplied to the plant material with an overhead Mandel track sprayerequipped with a 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 m² at a spray height of 18 to 20 inches (46 to50 cm) above average plant canopy height. Control plants were sprayed inthe same manner with the solvent blank.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After approximately 3 weeks, the condition of the testplants as compared with that of the untreated plants was determinedvisually and scored on a scale of 0 to 100 percent where 0 correspondsto no injury or growth inhibition and 100 corresponds to complete kill.

Colby's equation was used to determine the herbicidal effects expectedfrom the mixtures (Colby, S. R. 1967. Calculation of the synergistic andantagonistic response of herbicide combinations. Weeds 15:20-22.).

The following equation was used to calculate the expected activity ofmixtures containing two active ingredients, A and B:Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration asused in the mixture.

B=observed efficacy of active ingredient B at the same concentration asused in the mixture.

The compounds tested, application rates employed, plant species tested,and results are given in Tables 1-2.

TABLE 1 Synergistic Activity of Foliar-Applied Compound A Acid andClomazone Herbicidal Compositions on Weed Control in a Rice CroppingSystem. Visual Weed Compound Control (%) - A Acid Clomazone 19 DAAgae/ha gai/ha Obs Exp DIGSA 4.38 0 30 — 0 56 0 — 0 112 0 — 0 224 0 —4.38 56 45 30 4.38 112 40 30 4.38 224 45 30 LEFCH 17.5 0 55 — 0 56 0 — 0112 0 — 0 224 15 — 17.5 56 55 55 17.5 112 70 55 17.5 224 80 62 IPOHE4.38 0 0 — 8.75 0 10 — 0 112 20 — 0 224 20 — 4.38 112 15 20 8.75 112 6028 4.38 224 60 20 8.75 224 50 28

TABLE 2 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Clomazone Herbicidal Compositions on Weed Control in a Rice CroppingSystem. Compound Visual Weed A Benzyl Control (%) - Ester Clomazone 19DAA gae/ha gai/ha Obs Exp ECHCG 4.38 0 55 — 0 56 10 — 0 112 10 — 0 22410 — 4.38 56 85 60 4.38 112 80 60 4.38 224 75 60 ECHCO 4.38 0 65 — 0 5610 — 0 112 10 — 0 224 10 — 4.38 56 70 69 4.38 112 90 69 4.38 224 90 69LEFCH 17.5 0 30 — 0 56 0 — 0 112 0 — 0 224 15 — 17.5 56 45 30 17.5 11255 30 17.5 224 75 41 DIGSA Digitaria sanguinalis (L.) Scop.; crabgrass,large ECHCG Echinochloa crus-galli (L.) Beauv.; barnyardgrass ECHCOEchinochloa colona (L.) Link; junglerice IPOHE Ipomoea hederacea Jacq.;morningglory, ivyleaf LEFCH Leptochloa chinensis (L.) Nees; sprangletop,Chinese gae/ha = grams acid equivalent per hectare gai/ha = grams activeingredient per hectare Obs = observed value Exp = expected value ascalculated by Colby's equation DAA = days after application

Example II Evaluation of In-Water Applied Herbicidal Mixtures for WeedControl in Transplanted Paddy Rice

Weed seeds or nutlets of the desired test plant species were planted inpuddled soil (mud) prepared by mixing a shredded, non-sterilized mineralsoil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with apH of about 7.6 and an organic matter content of about 2.9 percent) andwater at a 1:1 volumetric ratio. The prepared mud was dispensed in 365mL aliquots into 16-ounce (oz.) non-perforated plastic pots with asurface area of 86.59 square centimeters (cm²) leaving a headspace of 3centimeters (cm) in each pot. Rice seeds were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic plugtrays. Seedlings at the second or third leaf stage of growth weretransplanted into 860 mL of mud contained in 32-oz. non-perforatedplastic pots with a surface area of 86.59 cm² 4 days prior to herbicideapplication. The paddy was created by filling the headspace of the potswith 2.5 to 3 cm of water. When required to ensure good germination andhealthy plants, a fungicide treatment and/or other chemical or physicaltreatment was applied. The plants were grown for 4-22 days in agreenhouse with an approximate 14 h photoperiod which was maintained atabout 29° C. during the day and about 26° C. during the night. Nutrientswere added as Osmocote® (17:6:10, N:P:K+minor nutrients) at 2 g per16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis tomaintain the paddy flood, and supplemental lighting was provided withoverhead metal halide 1000-Watt lamps as necessary. The plants wereemployed for testing when they reached the first through fourth trueleaf stage.

Treatments consisted of the acid or esters of4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylicacid (compound A) each formulated as an SC (suspension concentrate) andvarious herbicidal components alone and in combination. Forms ofcompound A were applied on an acid equivalent basis.

Forms of compound A (compound of formula I) tested include:

Other herbicidal components were applied on an active ingredient basisand consisted of clomazone formulated as Command® 3ME.

Treatment requirements for each compound or herbicidal component werecalculated based upon the rates being tested, the concentration ofactive ingredient or acid equivalent in the formulation, an applicationvolume of 2 mL per component per pot, and an application area of 86.59cm² per pot.

For formulated compounds, a measured amount was placed in an individual100 or 200 mL glass vial and was dissolved in a volume of 1.25% (v/v)Agri-Dex® crop oil concentrate to obtain application solutions. If thetest compound did not dissolve readily, the mixture was warmed and/orsonicated.

For technical grade compounds, a weighed amount can be placed in anindividual 100 to 200 mL glass vial and dissolved in a volume of acetoneto obtain concentrated stock solutions. If the test compound does notdissolve readily, the mixture can be warmed and/or sonicated. Theconcentrated stock solutions obtained can be diluted with an equivalentvolume of an aqueous mixture containing 2.5% (v/v) crop oil concentrateso that the final application solutions contain 1.25% (v/v) crop oilconcentrate.

Applications were made by injecting appropriate amounts of theapplication solutions with a pipetter, individually and sequentially,into the aqueous layer of the paddy. Control plants were treated in thesame manner with the solvent blank. Applications were made so that alltreated plant material received the same concentrations of acetone andcrop oil concentrate.

The treated plants and control plants were placed in a greenhouse asdescribed above and water was added as needed to maintain a paddy flood.After approximately 3 weeks the condition of the test plants as comparedwith that of the untreated plants was determined visually and scored ona scale of 0 to 100 percent where 0 corresponds to no injury or growthinhibition and 100 corresponds to complete kill.

Colby's equation was used to determine the herbicidal effects expectedfrom the mixtures (Colby, S. R. 1967. Calculation of the synergistic andantagonistic response of herbicide combinations. Weeds 15:20-22.).

The following equation was used to calculate the expected activity ofmixtures containing two active ingredients, A and B:Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration asused in the mixture.

B=observed efficacy of active ingredient B at the same concentration asused in the mixture.

Some of the compounds tested, application rates employed, plant speciestested, and results are given in Tables 3-4.

TABLE 3 Synergistic Activity of In-Water Applications of Compound A Acidand Clomazone Herbicidal Compositions on Weed Control in a Rice CroppingSystem. Compound A Acid Clomazone gae/ha gai/ha Obs Exp Visual WeedControl (%) - 21 DAA CYPRO 8.75 0 0 — 17.5 0 30 — 35 0 85 — 0 112 0 —8.75 112 30  0 17.5 112 30 30 35 112 100 85 Visual Weed Control (%) - 21DAA CYPDI 16 0 30 — 0 224 20 — 0 448 40 — 16 224 85 44 16 448 100 58Visual Weed Control (%) - 22 DAA SCPMA 16 0 0 — 32 0 0 — 64 0 30 — 0 44825 — 16 448 20 25 32 448 50 25 64 448 60 48

TABLE 4 Synergistic Activity of In-Water Applications of Compound ABenzyl Ester and Clomazone Herbicidal Compositions on Weed Control in aRice Cropping System. Compound A Benzyl Ester Clomazone gae/ha gai/haObs Exp Visual Weed Control (%) - 21 DAA SCPMA 4.38 0 0 8.75 0 0 17.5 00 0 112 0 4.38 112 20 0 8.75 112 20 0 17.5 112 100 0 Visual Weed Control(%) - 21 DAA CYPRO 8 0 70 — 16 0 95 — 32 0 90 — 0 448 0 — 8 448 95 70 16 448 100 95  32 448 100 90  Visual Weed Control (%) - 19 DAA SCPMA 8 00 — 16 0 0 — 32 0 0 — 0 670 0 — 8 670 10 0 16 670 10 0 32 670 90 0 CYPDICyperus difformis L. sedge, smallflower umbrella CYPRO Cyperus rotundusL. nutsedge, purple SCPMA Bolboschoenus maritimus (L.) Palla clubrush,sea gae/ha = grams acid equivalent per hectare gai/ha = grams activeingredient per hectare Obs = observed value Exp = expected value ascalculated by Colby's equation DAA = days after application

What is claimed is:
 1. A herbicidal composition, comprising: aherbicidally effective amount of (a) a compound of the formula (I):

or a C₁₋₄ alkyl, or benzyl ester, or an agriculturally acceptable saltof formula (I); and (b) clomazone or a salt thereof, and wherein (a) and(b) are present in the composition in a ratio such that the compositionexhibits synergy.
 2. The composition of claim 1, wherein (a) is a C₁₋₄alkyl ester of formula (I).
 3. The composition of claim 1, wherein (a)is a benzyl ester of formula (I).
 4. The composition of claim 1, wherein(a) is a carboxylic acid of formula (I).
 5. The composition of claim 1,wherein the weight ratio of compound of formula (I) or agriculturallyacceptable salt or ester thereof to clomazone is from about 1:153 toabout 1:1.
 6. The composition of claim 1, further comprising anagriculturally acceptable adjuvant carrier and/or safener.
 7. A methodof controlling undesirable vegetation, comprising the steps of:contacting a plant, wherein the plant is undesirable vegetation, or thelocus thereof, soil or water, wherein the soil or the water allows forthe growth of the undesirable vegetation, with a herbicidally effectiveamount of a combination comprising (a) a compound of the formula (I):

or a C₁₋₄ alkyl, or benzyl ester, or an agriculturally acceptable saltof formula (I); and (b) clomazone or a salt thereof, wherein (a) and (b)are present in the combination in a ratio such that the combinationexhibits synergy for the control of undesirable vegetation in at leastone of a direct-seeded plant or a water seeded plant or a transplantedplant selected from the group consisting of: rice, cereals, wheat,barley, oats, rye, sorghum, and corn/maize crop.
 8. The method of claim7, wherein the undesirable vegetation is immature.
 9. The method ofclaim 7, wherein the (a) and (b) are applied to water.
 10. The method ofclaim 9, wherein the water is part of a flooded rice paddy.
 11. Themethod of claim 7, wherein the (a) and (b) are applied pre-emergentlyand/or post-emergently to the undesirable vegetation in the crop. 12.The method of claim 7, wherein the undesirable vegetation is controlledin glyphosate-, 5-enolpyruvylshikimate-3-phosphate synthase inhibitor-,glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-,pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-,aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetylCoA carboxylase inhibitor-, imidazolinone-, sulfonylurea-,pyrimidinylthiobenzoate-, triazolopyrimidine-,sulfonylaminocarbonyltriazolinone-, acetolactate synthase oracetohydroxy acid synthase inhibitor-, 4-hydroxyphenyl-pyruvatedioxygenase inhibitor-, phytoene desaturase inhibitor-, carotenoidbiosynthesis inhibitor-, protoporphyrinogen oxidase inhibitor-,cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubuleinhibitor-, long chain fatty acid inhibitor-, fatty acid and lipidbiosynthesis inhibitor-, photosystem I inhibitor-, photosystem IIinhibitor-, triazine-, or bromoxynil-tolerant crops.
 13. The method ofclaim 12, wherein the tolerant crop possesses multiple or stacked traitsconferring tolerance to multiple herbicides.
 14. The method of claim 7,wherein the undesirable vegetation comprises a herbicide resistant ortolerant plant.
 15. The method of claim 14 wherein the resistant ortolerant plant is resistant or tolerant to multiple herbicides ormultiple herbicide modes-of-action.
 16. The method of claim 14, whereinthe resistant or tolerant plant is resistant or tolerant to acetolactatesynthase or acetohydroxy acid synthase inhibitors, photosystem IIinhibitors, acetyl CoA carboxylase inhibitors, synthetic auxins, auxintransport inhibitors, photosystem I inhibitors,5-enolpyruvylshikimate-3-phosphate synthase inhibitors, microtubuleassembly inhibitors, fatty acid and lipid synthesis inhibitors,protoporphyrinogen oxidase inhibitors, carotenoid biosynthesisinhibitors, long chain fatty acid inhibitors, phytoene desaturaseinhibitors, glutamine synthetase inhibitors,4-hydroxyphenyl-pyruvate-dioxygenase inhibitors, mitosis inhibitors,cellulose biosynthesis inhibitors, herbicides with multiplemodes-of-action, quinclorac, arylaminopropionic acids, difenzoquat,endothall, or organoarsenicals.